Bailey Pumfleet

Overview

Bailey Pumfleet is the Co-founder and CEO of Cal.com, a company that provides open-source calendar scheduling solutions. Under his leadership, Cal.com has achieved significant milestones, including raising over $32 million in seed and Series A funding rounds, attracting more than 150,000 users, and expanding the team to 25 employees. The company has been recognized as one of the 30 early-stage startups in 2025 most likely to become tech's next unicorns, with a valuation of $175 million and total funding of $32.5 million. Cal.com has attracted investments from notable firms such as New Enterprise Associates, Sapphire Ventures, Lightspeed Venture Partners, and Scott Galloway. Bailey's entrepreneurial journey began at the age of 18, when he co-founded Cal.com and secured a $25 million Series A funding round, demonstrating his ability to execute complex ideas effectively. His leadership and strategic vision have been instrumental in Cal.com's rapid growth and success in the competitive technology startup landscape. Bailey's approach to building a successful startup emphasizes the importance of hiring individuals with a founder-level drive, even if they are not founders themselves. He values candidates who have demonstrated hustle and determination, focusing on team fit and proactive communication, especially in remote work environments. This philosophy reflects his commitment to fostering a strong, motivated team that aligns with the company's mission and values. His leadership style and hiring practices have contributed to Cal.com's dynamic and innovative culture, positioning the company as a significant player in the open-source scheduling infrastructure sector. Through his role at Cal.com, Bailey Pumfleet continues to influence the early-stage technology startup ecosystem, driving innovation and growth in the scheduling solutions market. His dedication to providing accessible and efficient scheduling tools has resonated with a wide user base, solidifying Cal.com's position as a leading provider in its field. His ongoing efforts aim to connect a billion people by 2031, reflecting his long-term vision and commitment to impactful technological advancement.

Investment Focus

• Innovative technology solutions
• Scalable business models
• Strong founding teams

Portfolio Companies